Windley Classic 22 Sailboats for Sale

Stuart Windley·1989·Classic Yachts Inc.
Approximate drawing

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Hull Type
Monohull · centerboard
Rig
Fractional Sloop
LOA
21.67' · 6.61 m
Disp.
2,300 lbs · 1,043 kg
First year
1989

The Windley Classic 22 is an American trailerable sailboat, a 21foot67inch cruiser designed by Stuart Windley and first built in 1989 by Classic Yachts in Chanute, Kansas. It emerged as a development of the Gloucester 22 and was originally marketed by the builder simply as the Classic 22, a name now usually written as the Classic 22 (Windley) to keep it distinct from an unrelated 1962 design of the same name. Production has since ended, but the boat remains a recognizable small coastal cruiser with a retractable centerboard and a genuinely trailerable footprint.

Market snapshot

Median asking · 12 mo
Asking price
Recent listings · 90 d
Listed for sale
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Global market

Recent Listings

1 for sale · showing 10 newest

Windley Classic 22 Buyer's Guide

The Windley Classic 22 is a small American trailerable cruiser designed by Stuart Windley and built by Classic Yachts starting in 1989, with production now closed. On the used market it presents as a 21-foot-67-inch coastal cruiser with a retractable centerboard and an outboard motor, aimed at buyers who want a boat they can tow, launch, and camp aboard without the overhead of a fixed-keel inboard design.

Layouts on the Used Market

Windley Classic 22 boats carry the same 21-foot-67-inch hull with an 8-foot beam and a cabin conceived as a coastal cruiser. The retractable centerboard gives a retracted draft of 1.67 feet for trailering and a extended draft of 4.92 feet under sail, so check that the board in any example moves freely and the trunk is dry. The outboard motor means no inboard compartment to survey, but confirm the transom mount is sound.

Equipment and Common Upgrades

The design uses an outboard motor for propulsion, leaving the hull interior open for cabin space. Trailerable nature means a roadworthy trailer is essential equipment.

What to Inspect

The Classic 22 has a solid fiberglass hull and deck with wood trim, so check the wood trim for rot at joints and the solid laminate for old gelcoat crazing. The fixed stub keel with retractable centerboard means the trunk and pivot hardware deserve attention: confirm the board moves freely and the trunk shows no staining that would signal water ingress. With an outboard engine type, inspect the transom mount and wiring for corrosion.

Availability and Buyer's Takeaway

Windley Classic 22 boats appear on the open market without documented regional concentration.

  • Confirm centerboard trunk is dry and free
  • Check wood trim for rot at joints
  • Test outboard mount and wiring
  • Verify trailer suitability for 2,300 lb

Comparable models

Similar length, displacement, and era. Open a row to compare that model's market page.

Similar boats to compare

2 similar designs
ModelLOAMedian askListings · 12 moActive · 90 d
Catalina 2223.83'$ 6,5007922
Hurley 2222'$ 3,384155

Frequently asked questions

01What should I look at instead of a Windley Classic 22?+
Comparable models include Catalina 22, Hurley 22. Use the comparison table above to check pricing and availability.